Re: can I afford to continue sailing
I'm in a similar situation (30s, married, young kid, not rich), but my wife so far has been supportive of the boat.
We justify the cost of owning the boat in a few ways. For one, spending the weekend on the boat is pretty cheap entertainment. We pack our food and spend zero money once we leave the mooring. Next summer we plan to take about 10 days and cruise our local waters, whereas before the boat we'd spend a few thousand on a summer vacation somewhere.
Perhaps even more important, it's a way to do something fun together as a family. Wife is not crazy about sailing itself, but she does love spending a weekend as a family on the boat. Consequently, a day on the boat with the family might only entail a few hours of sailing, and many more hours at anchor swimming, reading, relaxing, etc.
Maybe that will give you some ideas to work with.... Good luck!